The Idea of a Woman

What color are my panties?

What style and color are my panties?

My girlfriend Stephanie is vacating the apartment we once shared on the Lower East Side, so what to do with all my stuff I left behind when I moved to Europe last year?  I don’t remember what’s there exactly — probably lots of fashionable clothes that immediately became unfashionable the week after I bought them.  Plus tons of old underwear, pantyhose, camisoles and such.

But I don’t want to tell Steph to simply toss them in the trash, for they’re money in the bank!  Like Bitcoins, a form of international currency!! And like vintage collectibles, the older and more worn, the more valuable they seem to be!!!

I’ve had some experience with men in the past fantasizing about — and fetishizing — my undies, but only recently have I come to understand what an incredible business opportunity they represent.

When I worked as an escort, guys would sometimes bring me lingerie to wear while we had sex, and then take it back home with them as a trophy of sorts.  And one guy, a regular, would wear panties himself to our encounter, then take them off, ask me to then put them on; afterwards, he would use them to masturbate in.  Feeling the silky softness around his shaft was infinitely more fun, I guess, than feeling it deep down my throat.

I’m not being critical or judgmental.  For I’ve often cum in my own panties myself.  When I use a vibrator, in fact, it just feels somehow sexier to leave my panties on.  Anyway….

Over the last few months a bunch of Facebook friends/followers/fans have offered big bucks for items from my lingerie chest.  I don’t even have to freshly wash them — the more spoiled, apparently the better!  I’m beginning to think I’m sitting (both literally and figuratively) on a gold mine!

Come to think about it, maybe the intimates I wear — conveying the idea of me — is so much better than the reality of me.  Hosiery, thongs and bikinis never bitch and complain, never need selfish satisfaction.  They exist just for your pleasure….yours alone.

So take my poll and send me a offer…. opening bid on my bright orange thong, for example, starts at $50!

Men I Have Known: Chapter 1

Now that I'm respectable, I can reflect....

Looking “respectable” belies my memories….

The turning of the New Year invites reflection; and the thought occurs that time’s passage has, for me, been punctuated not with the ticking of clocks or turning of calendar pages but, rather, with all the different lovers I’ve known.  “Lovers” might be too grand a word, for many of these men I’ve known, when I was escorting, for only an hour or so.  And some I’ve come to know now only virtually, via the Internet.

Whatever I call them, they are someone else’s son, brother, father, boyfriend, husband even.  It’s said that, no matter how intimate, you can never really, really know someone.

So I may not be privy to the day-to-day life of the man sitting across from you at the dinner table right now, but I know his secrets, things you’ll never know.

Take Bukkake Bob, for instance.  That’s what I called him, and not just behind his back.  I made him laugh (not just cum).

All he wanted to do was splash his hot, gooey ejaculate all over my face and titties.  I didn’t have to do anything — not even suck — just kneel there, with my face uplifted and smiling expectantly.  Sometimes I would wag my tongue (this was long before Miley Cyrus’s iconic move) to gesture how much I wanted it, craved it — to feel and taste the splash of his cum.

Once a week, like clockwork, we would meet to perform this ritual, sometimes in my apartment, sometimes in a motel room, sometimes in his huge SUV.

Then one evening, when I had on a lot of makeup (for I was to go on a fancy dinner date with another guy an hour later), I tilted my head ever so slightly just as Bob shot his wad.  So most of what he shot ended up on the floor.

“What happened?” His scream sounded truly anguished.

“I didn’t want to totally ruin my makeup, sweetie.”  I said matter-of-factly.

“Well, you’ve now ruined everything,” he announced, and I never saw him again.

What more can I say?

Harem Girl (Part 2): Pros and Cons

Which one's the eunuch?

Which one’s the eunuch?

Is it because I was born a boy that I am now Super Rational Girl?  What I mean to say is: Do I still put too much stock in reason as opposed to emotion — always being analytical as opposed to just listening to my newfound woman’s intuition?  Who knows?  

But whatever the explanation, my brain just won’t let me be the bimbo that I want to be!  So as much as I found appealing the idea of actually joining a real-life harem, I quickly made a mental calculation of all the pluses and minuses:

On the plus side, was the money, obviously, that I had been offered.  But perhaps even more enticing was the chance for the uniquely feminine camaraderie being just one of the harem girls — being pledged into a secret sorority, as it were!

A definite minus, however, was the undefined, open-ended nature of what I was getting into — would I be able to leave when I wanted, or was I potentially enslaving myself?  Sex slave sounds sexy…until it’s not!

But before I even got to dress up in my harem costume, or whatever, I would have to have an orchiectomy, my would-be master had insisted.  I’d still be a pre-opt Tgirl, but minus my two balls!  This prospect, too, had its own balance sheet:

On the pro side, no longer would I have to take a daily testosterone blocker.  Henceforth, my good, old faithful estrogen patch would be all I ever need.

On the con side, however, if I ever go through with the actual surgical sex-change, some of the best doctors prefer that the scrotum be fully in tact — providing more material to work with in fashioning a vagina.

And perhaps most important: I think a pre-opt Tgirl, like a candy bar, is just plain sexier with nuts!  That’s yummy me!

The Serious Shemale

Instead of short shorts...what if my latest fashion purchase was referred to as  "sea-level-rise-induced-by global-warming" hotpants...would I then begin to be taken more seriously?

Instead of short shorts….

….What if my latest fashion purchase was referred to as “sea-level-rise-induced-by-global-warming hotpants,” would I then begin to be taken more seriously?  Not that I pretend to be a real intellectual or anything, but still….

Why don’t people take us shemales seriously?  Is it because we’re perceived as boys who just want to be bimbos?  The truest and most authentic of bimbos who’re only interested in and motivated by sexy, dolled-up clothes — and, of course, sex itself?

But “regular” transsexuals — those who follow through on SRS (sex reassignment surgery) — are often treated with the utmost dignity and respect.  (That is, obviously, except among Philistines and homophobes!)

Not only are transsexuals like Jan Morris (the travel writer and essayist) and Jennifer Finney Boylan (the English professor and author) greeted with respect, even awe — but also are considered intellectually serious thinkers worth paying attention to.

Part of the reason, of course, is that shemales are often associated with porn and prostitution.  While I personally have never done porn, I readily confess to having worked as an escort (just a euphemism for prostitute!)  But getting paid for sex (or often simply my companionship) did not deter my intellectual curiosity.  To the contrary, I read more now — and am better-informed — than I’ve ever been.  And each of my clients was like a richly nuanced character in the very greatest novels and/or a deeply layered case study in the most intense Freudian psychoanalysis.

My mission, then, is clear.  It’s simple.  You can guess what it is!

10 Stupid John Tricks: A Pro’s Pet Peeves

sex worker1.  Like Congressman Weiner (still can’t believe his name!), sexting a picture of your penis…. As if girls care what it looks like! (“Feels like” is another matter.)

2. On the subject of Congress…. Lecturing me about how clever and sexy the House Republicans are.

3. Running my Wolford’s hosiery.

4. Wanting to wear my panties.

5.  Taking my panties with you as a souvenir.

6.  Screaming out your dog’s name when you cum (and we’re not even doing it doggie style).

7.  Telling me to play with a second-hand sextoy that you brought along.

8.  Taking the entire one-and-one-half-hour appointment to cum.

9. Complaining you’ll go limp if you have to wear a condom.

10. Texting your wife while I’m giving you the best head you’ve ever had.

Dirty Little Secret

tampon trainer Serendipity! Think of how many splendid things happen in life because of serendipity! Sort of like Kismet…. So much better and more romantic than mere biological necessity….

I remember it as if yesterday, every detail, told and retold in my mind so often that it’s become myth-like in my creation: the first time, the very first time, I bought tampons!

Why, oh why, would a “special girl” like I ever need to buy tampons?  Wrong question.  As with any unnatural act or unspeakable practice, it has very little to do with “need.”  Rather, the correct frame is this: Why would I WANT to buy tampons? And the answer to that is really quite easy:

It happened in my early days of transitioning, always watchful that I wouldn’t “pass,” when one afternoon I was pushing a shopping cart full of necessities at the local grocery store and caught out of the corner of my eye an older woman staring at me. I didn’t acknowledge her gaze, but, instead, pretended to read the various yogurt labels in the refrigerated display case.  She continued to stare as I pushed the cart toward the check-out.  The quickness of my gait no doubt betrayed my nervousness…and confirmed her doubts.

And then…and then…I happened to spot the display for Tampax   Without really thinking, I found my hand casually reaching for a super-sized box and dropping it in my cart.  A few more steps brought me to the check-out lane, and the stalker had vanished.

Of course, once I got home in the privacy of my bedroom, since I had paid for them, I had to try them out — using the only hole I had. I’ll mercifully spare you the details of my initial experimentation, but….

I became addicted.  I bought boxes and boxes of tampons, testing all makes and sizes.  I would go through five or six tampons a day. To feed my addiction, I bought tampons at any store that sold them, so that the clerks at my neighborhood grocery wouldn’t think I had some kind of serious gynecological problem.

For an anal sex virgin, as I was then, the Playtex “Gentle Glide” — yes, most especially the aptly named Gentle Glide! — provided perhaps the friendliest rectal dilator possible for bottom training.  It opened the way or primed the pump (which is the better metaphor?) for butt plugs and ever bigger dildos and, yes, of course, eventually, the real thing.

And more, so much more: I found that having a tampon inside of me, underneath my panties and hose, when I went out on a date made me feel so much more naturally, womanly receptive — for the real thing later that evening.  And just like a real woman getting ready for the real thing — before I would let his hard cock enter me — I would excuse myself to go quickly to the bathroom, to make myself ready.  After discreetly disposing of the tampon, I never felt so clean — my butt-pussy, that is.  But the moisture-absorbing tampon also made it feel unusually dry, of course, so I would always be prepared by bringing ample supplies of lubricant in my purse.

There!  Now you know just about all my dirty little secrets.

But not quite all….

Becoming a Shemale Hooker, Chapter 6

profileWhat’s the hardest thing you have ever had to do?  Learn Latin?  Run to win a 5-K race?  Play hostess at a Black Tie dinner party?  Perform the starring role in your school’s “The Nutcracker?”  Execute a French manicure on your very own nails?

For me, the very, very, very hardest thing is putting a rubber on a limp penis.  I’ve only had to do it once (thank God!), and that occurred during my very first date as a shemale escort.  It was a truly unique skill I developed on the spot.

I could see him go limp as I fumbled in my purse for the condom.  (Have you ever been able easily or quickly to find something in your purse when you need it most, when time is of the absolute essence?)

At first I didn’t think it would be a problem.  All I had to do was lightly brush his sensitive skin with my finely manicured, sexy fingernails, right?   After all, just moments earlier, his cock , though tiny, had been explosively erect.  But that was then; this was now.

Then he had been fondling my own cock, which I preferred to think of as just an oversized clitty.  To be frank, my clitty didn’t like the too rapt attentions of his monotonous, and rather rough, hand motions.  The very tip of my big clitty was actually getting sore; my pantyhose felt like sandpaper.

If I could just make him cum, I would have earned my money, and I could leave.

I pressed the rubber against the head of his penis and clamped the rolled-up sides with my fingers.  Then I took my tongue so that it tasted the rubber tip.  Flicking my tongue, as I so desperately had hoped, gradually stiffened what I held between my fingers — sufficient to gain purchase to unroll the condom.  As it unrolled, my lips parted and slid over the tip and down the ever lengthening, but still short, shaft.

Now my lips and throat and bobbing head could work their gliding magic, and they did.  But, from Mr. Jackson, there were no quickening thrusts and volcanic eruptions, as with a younger man.  Instead, when he came, I heard a barely perceptible grunt and felt the condom inflate like a tiny balloon.  The texture and consistency felt like an over-ripe melon about to melt and get messy in my mouth.

When I left his office, he said a very formal thank-you, and I noticed that all around the walls were hanging pictures of his wife and children and grandchildren (I could only presume, I didn’t dare ask): mute witnesses to the display of his extramarital activities with a shemale.  He must not have cared.

I only cared what he would tell Marvin, my pimp.  Mr. Jackson – I mean Jack (I wasn’t supposed to know his last name) – was one of Marvin’s regulars. What kind of report card would I be given?  I knew it would not be an “A,” because I had dissuaded him from doing what he really wanted – to play with my big clitty.   So was I failure?  Would Jack ever want to pay for me again?  A satisfied, repeat customer?

Or would my very first trick also be my last?

Becoming a Shemale Escort: Chapter 5

secrets7He didn’t try to kiss me.  He didn’t grab my boobs.  He didn’t rip my clothes off, or even undress himself.  Instead, Jack asked me to sit on the edge of the desk and hike my skirt up and spread my legs. He then rolled the desk’s over-sized matching chair toward me and, like an old frayed teddy bear, plopped down in it. His face betrayed a bashful grin as he rolled the chair closer and closer.

I really had no idea what would happen next. But I was no longer afraid, just really curious. So far, at least, if I had to describe him, it would be, as I already mentioned, as an old teddy bear. Gentle but not necessarily cuddly (he was too ugly for that!). And what he was now doing — rolling the chair every closer so that his face was pressed closer and closer to my panty-less crotch — sparked some involuntary whimsy from my lips:

“I feel like my body is a computer and you’re about to start typing on the keyboard!” I laughed.  And he did, too — a hoarse, breathy laugh that tickled my scrotum (yes, his face was that close!).

He nuzzled his face ever tighter against my male genitals, already pressed tight against the flesh-colored pantyhose that he had instructed me to wear. Why he had been so insistent that I wear no panties, I now understood.

If he was expecting me to get hard…well, he would have been within his rights to want a refund. I glanced down and tried to see if he was getting hard — that was all that counted, right? — and I thought/hoped I detected a growing bulge in his pants. Maybe just wishful thinking?

I wanted and needed for Jack to be happy…so that Marvin would be happy…so that I wouldn’t be fired. Most of all, I wanted this moment to be over with, in a satisfactory manner, so that I could feel like I’d actually earned the money. Yes, I wanted to make sure Jack got his satisfaction. Pride in my new identity was at stake.

Against the nylon of my hose, his rough thumb began to make circular motions around the head of my still flaccid penis.  He did it so much and so hard, I was beginning to feel painfully sore and inflamed at the head of my urethra.  I had to change the subject of his attention.

“Let me suck your cock,” I suddenly said.

“With Marvin’s other girls, I always suck their cocks.”  He seemed puzzled.

“Well, give me a chance,” I begged. “You might be surprised. You might really like it. I give really good head.”

Becoming a Shemale Hooker: Chapter 4

callgirl3At first around my waist, gradually sliding down to my butt, Jack’s hand guided me through what seemed like countless doors and long corridors.  The click of my heels and the sway of my hips displayed a confidence I had not yet earned.  Like a virgin acting like a sexpot, down deep I knew I was a fraud, a fake, just a wanabee whore.  It wouldn’t take much to reignite the worries and fears I had felt initially when Jack’s creepy telephone voice was booking our date.

So when Jack ushered me, the nervous Nellie, into the inner sanctum of his executive suite and locked the door behind us, one of my heels snagged the edge of an Oriental carpet. I would have fallen had Jack not steadied me.  All the lady-like poise I had spent months, even years, cultivating quickly melted into embarrassment…and, yes, fear.

“Maybe I should call Marvin…” I stammered and reached into my purse for the cellphone. “… And tell him I’m here.”

“No need to do that, Joyce.”  He handed me an unsealed envelope.  “Put this in your purse instead.”  My fingers opened the envelope and flipped through the bills — four $100’s and one $50.  Just as Marvin — the escort service owner and so, yes, my pimp —  had said it would work!  My estrogen-patch-addled bimbo brain didn’t even have to remember to ask for the money!

What exactly was Jack buying for $450?  I wasn’t yet sure.  That was my appointment rate set by Marvin.  For that amount, the client could have up to one and one-half hours of my precious time.  If the client wanted additional time, it would be at the $300 hourly rate.  Overnight rates could be negotiated.

Everything had to be prepaid, either by credit card over the phone with Marvin or by handing cash directly to me.  If the latter, I would deposit Marvin’s one-third directly into his bank account the next morning at a bank branch most convenient to me.

I’ll tell you more about Marvin later, but at that particular moment I was in awe.  He had thought of everything — as slyly clever as any Wall Street hedge fund manager.  By paying upfront, the client could never be undercover police because that would be entrapment.  And by coordinating all the logistics of the appointment through Marvin’s office, I was reasonably safe: if I didn’t report in by phone in exactly one and one-half hours, Marvin would send one of his assistants looking for me.

Marvin had the address.  He had the client’s phone number, maybe even credit card number.  Marvin knew everything.  My fate was in his hands.  Suddenly I had a glimpse of the legendary power of a pimp:  Marvin had become my God-like protector.

Of course, Marvin at this very moment could not prevent Jack from raping me, killing me, then cutting me up into tiny pieces.  But if Jack was rational, he knew he would never get away with it….right?

Becoming a Shemale Hooker: Chapter 3

callgirl3Just as Mr. Jackson had instructed on the phone (in a hoarse and heavy-breathing voice), I pulled my car into the dark and mostly deserted office parking lot… and headed toward the illuminated place under the lamp-post.  There I was to park — in the spotlight under the lamp-post.  The phallic symbolism — I couldn’t help but smile — relieved at least some of my anxiety.  My next instructions were these:

Turn the car engine off.  Turn on the car’s inside lights.  Look in the rear-view mirror and start touching up my makeup, specifically my lipstick.  Wait for my cell to ring, which it now did just moments after I had deposited my lipliner back in my purse.

“Yes, Mr. Jackson…. Yes, Mr. Jackson…. Yes, of course, I want to make you happy.”   After his abrupt goodbye, I proceeded to do exactly as I had just been told:

Make believe I’m just a normal businesswoman arriving at a real job. Open the car door.  Stay seated, but swivel my legs so that my heels are on the pavement.  Make sure that my skirt is hiked up, so that an observer from the office building can see my crotch.

“Wear no panties!” he had earlier commanded.  Now I began to understand.  And I followed precisely the rest of his instructions:

Pretend I’m unaware of either the observer or the fact that my crotch is showing.  When I stand up, feint surprise that my skirt is hiked up so high; quickly tug it down to mid-thigh; look around, embarrassed, to make sure no one has seen me; then walk briskly, as if late for work, to the office entrance.

Buzzed through security, I then took the elevator to the second floor. There waiting for me as I exited the elevator was Mr. Jackson. I can’t describe exactly the man I had expected as my very first “John,” but he definitely wasn’t it!  And his voice no longer made me tremble:

“You’re beautiful,” he said — the binoculars still in hand that he had obviously used to spy on me arriving in the parking lot. “The agency’s photos don’t do you justice.”

“Thank you, Mr. Jackson.”

“Just call me Jack,” he said, holding the door open for me to step into Suite 210.